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【结 构 式】

【分子编号】69121

【品名】6-methoxy-7-(3-morpholinopropoxy)quinolin-4-ol

【CA登记号】 

【 分 子 式 】C17H22N2O4

【 分 子 量 】318.37276

【元素组成】C 64.13% H 6.97% N 8.8% O 20.1%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XXXI)

Alkylation of 4’-hydroxy-3’-methoxyacetophenone (XVII) with benzyl bromide by means of K2CO3 in DMF gives benzyl ether (XVIII), which is reacted with fuming HNO3 and concentrated H2SO4 in cold CH2Cl2 to afford 4’-benzyloxy-5’-methoxy-2’-nitroacetophenone (XIX). After reduction of the nitro group of compound (XIX) using iron powder and ammonium formate in refluxing H2O/toluene, the resulting 2-aminoacetophenone derivative (XX) cyclizes with ethyl formate (XXI) in the presence of NaOEt in DME, providing 7-benzyloxy-6-methoxy-4-quinolinol (XXII). Finally, quinolinol (XXII) is treated with trifluoromethanesulfonyl chloride in the presence of DMAP and 2,6-lutidine in cold CH2Cl2 .

1 Deschamps, N.M., Martin, M.T., Monteith, M.J., Zhou, X. (GlaxoSmithKline Inc.). Preparation of a quinolinyloxydiphenylcyclopropanedicarboxamide. US 2010081805, WO 010036831.
2 Wilson, J., Zuberi, S., Naganathan, S., Goldman, E., Kanter, J. (Exelixis, Inc.). Methods of preparing quinoline derivatives. WO 2010056960.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXIVa) 22605 4-(3-Chloropropoxy)-3-Methoxyacetophenone;3-(4-Acetyl-2-methoxyphenoxy)propyl chloride;1-(4-(3-chloropropoxy)-3-methoxyphenyl)ethanone;1-[4-(3-chloropropoxy)-3-methoxyphenyl]-1-ethanone 58113-30-7 C12H15ClO3 详情 详情
(XXIVb) 69115 1-(4-(3-bromopropoxy)-3-methoxyphenyl)ethanone   C12H15BrO3 详情 详情
(XXVa) 69117 1-(4-(3-chloropropoxy)-5-methoxy-2-nitrophenyl)ethanone   C12H14ClNO5 详情 详情
(XXVb) 69116 1-(4-(3-bromopropoxy)-5-methoxy-2-nitrophenyl)ethanone C12H14BrNO5 详情 详情
(VI) 69105 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinoline;4-(3-((4-chloro-6-methoxyquinolin-7-yl)oxy)propyl)morpholine   C17H21ClN2O3 详情 详情
(XVII) 22604 1-(4-hydroxy-3-methoxyphenyl)-1-ethanone;Acetovanillone;4’-hydroxy-3’-methoxyacetophenone;1-(4-hydroxy-3-methoxyphenyl)ethanone 498-02-2 C9H10O3 详情 详情
(XXI) 16602 ethyl formate 109-94-4 C3H6O2 详情 详情
(XXIII) 10358 1-Bromo-3-chloropropane 109-70-6 C3H6BrCl 详情 详情
(XXVI) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(XXVII) 69118 1-(5-methoxy-4-(3-morpholinopropoxy)-2-nitrophenyl)ethanone   C16H22N2O6 详情 详情
(XXVIII) 56891 1,3-propanediol cyclic sulfate;1,3,2-dioxathiane 2,2-dioxide;1,3-Propylene sulfate 1073-05-8 C3H6O4S 详情 详情
(XXIX) 69119 4’-(morpholinopropoxy)acetophenone;1-(3-methoxy-4-(3-morpholinopropoxy)phenyl)ethanone   C16H23NO4 详情 详情
(XXX) 69120 1-(2-amino-5-methoxy-4-(3-morpholinopropoxy)phenyl)ethanone   C16H24N2O4 详情 详情
(XXXI) 69121 6-methoxy-7-(3-morpholinopropoxy)quinolin-4-ol   C17H22N2O4 详情 详情
(XXXII) 20360 methyl(phenyl)formamide;N-Methylformanilide;N-Formyl-N-methylaniline;Methylphenylformamide;N-methyl-N-phenylformamide;N-Methyl-N-formylaniline;N-Formyl-N-methylaniline 93-61-8 C8H9NO 详情 详情
Extended Information